DE69715911T2 - Pestizide 1-arylpyrazole - Google Patents
Pestizide 1-arylpyrazoleInfo
- Publication number
- DE69715911T2 DE69715911T2 DE69715911T DE69715911T DE69715911T2 DE 69715911 T2 DE69715911 T2 DE 69715911T2 DE 69715911 T DE69715911 T DE 69715911T DE 69715911 T DE69715911 T DE 69715911T DE 69715911 T2 DE69715911 T2 DE 69715911T2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- trifluoromethyl
- alkyl
- dichloro
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000575 pesticide Substances 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 189
- 125000000217 alkyl group Chemical group 0.000 claims description 183
- 239000000203 mixture Substances 0.000 claims description 142
- 229910052739 hydrogen Inorganic materials 0.000 claims description 123
- 239000001257 hydrogen Substances 0.000 claims description 121
- 125000001188 haloalkyl group Chemical group 0.000 claims description 87
- -1 carboxy, cyano, aminocarbonyl Chemical group 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 57
- 150000002367 halogens Chemical group 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 241000607479 Yersinia pestis Species 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 101150018444 sub2 gene Proteins 0.000 claims description 13
- HUFSITFCVJWWGD-UHFFFAOYSA-N N-[[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]hydroxylamine Chemical compound N1=C(C=NO)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HUFSITFCVJWWGD-UHFFFAOYSA-N 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000003435 aroyl group Chemical group 0.000 claims description 12
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 11
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000006519 CCH3 Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000002923 oximes Chemical class 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims description 6
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 125000005182 hydroxyalkylcarbonyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- NMJMZHWEEYJTQH-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-n'-methoxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound NC1=C(S(C)=O)C(C(=N)NOC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NMJMZHWEEYJTQH-UHFFFAOYSA-N 0.000 claims description 4
- 102220535958 Dynein axonemal intermediate chain 4_R17S_mutation Human genes 0.000 claims description 4
- 125000004700 alkyl sulfonyl alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 4
- JQOACNONRUXOSI-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-formyl-N'-hydroxy-4-(trifluoromethylsulfanyl)pyrazole-3-carboximidamide Chemical compound O=CC1=C(SC(F)(F)F)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl JQOACNONRUXOSI-UHFFFAOYSA-N 0.000 claims description 3
- XZHJFPHRSFLSJH-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-5-(hydroxyiminomethyl)-4-(trifluoromethylsulfanyl)pyrazole-3-carboximidamide Chemical compound ON=CC1=C(SC(F)(F)F)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XZHJFPHRSFLSJH-UHFFFAOYSA-N 0.000 claims description 3
- DERHJHAJLHIJPZ-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(2-ethylsulfonylethoxyiminomethyl)-4-methylsulfinylpyrazol-3-amine Chemical compound NC1=C(S(C)=O)C(C=NOCCS(=O)(=O)CC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DERHJHAJLHIJPZ-UHFFFAOYSA-N 0.000 claims description 3
- ZQXAPXWLKJJKPL-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methoxyiminomethyl)-4-(trifluoromethylsulfanyl)pyrazol-3-amine Chemical compound NC1=C(SC(F)(F)F)C(C=NOC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZQXAPXWLKJJKPL-UHFFFAOYSA-N 0.000 claims description 3
- YVKFJKFLBGMIBM-UHFFFAOYSA-N 2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methoxyiminomethyl)-4-methylsulfinylpyrazol-3-amine Chemical compound NC1=C(S(C)=O)C(C=NOC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YVKFJKFLBGMIBM-UHFFFAOYSA-N 0.000 claims description 3
- YFJLYWROTSOALE-UHFFFAOYSA-N 2-[[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino]oxyacetic acid Chemical compound N1=C(C=NOCC(O)=O)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YFJLYWROTSOALE-UHFFFAOYSA-N 0.000 claims description 3
- ZTYUYJGHROEUOE-UHFFFAOYSA-N 3-[[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino]oxypropanenitrile Chemical compound N1=C(C=NOCCC#N)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZTYUYJGHROEUOE-UHFFFAOYSA-N 0.000 claims description 3
- VREADUYBUNLTAP-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-(trifluoromethylsulfinyl)pyrazole-3-carboximidamide Chemical compound NC1=C(S(=O)C(F)(F)F)C(C(=NO)N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VREADUYBUNLTAP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006845 Michael addition reaction Methods 0.000 claims description 3
- HLQHKSOTOHOERT-UHFFFAOYSA-N N-[[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]hydroxylamine Chemical compound N1=C(C=NO)C(S(=O)C)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HLQHKSOTOHOERT-UHFFFAOYSA-N 0.000 claims description 3
- QWLVAEKWAUDDDA-UHFFFAOYSA-N N-[[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylsulfanylpyrazol-3-yl]methylidene]hydroxylamine Chemical compound N1=C(C=NO)C(SC)=C(C)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QWLVAEKWAUDDDA-UHFFFAOYSA-N 0.000 claims description 3
- VAPFDOPZPRHNRW-UHFFFAOYSA-N N-[[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylsulfinylpyrazol-3-yl]methylidene]hydroxylamine Chemical compound CC1=C(S(C)=O)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VAPFDOPZPRHNRW-UHFFFAOYSA-N 0.000 claims description 3
- GBSDTGATUBNQTH-UHFFFAOYSA-N N-[[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-4-methylsulfonylpyrazol-3-yl]methylidene]hydroxylamine Chemical compound CC1=C(S(C)(=O)=O)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GBSDTGATUBNQTH-UHFFFAOYSA-N 0.000 claims description 3
- DBEKSNQGWSLCEB-UHFFFAOYSA-N [[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino] acetate Chemical compound NC1=C(S(C)=O)C(C=NOC(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DBEKSNQGWSLCEB-UHFFFAOYSA-N 0.000 claims description 3
- VEHHQIHBEVMLCQ-UHFFFAOYSA-N [[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino] n-methylcarbamate Chemical compound NC1=C(S(C)=O)C(C=NOC(=O)NC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VEHHQIHBEVMLCQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004703 alkyl carbonyl aminoalkyl carbonyl group Chemical group 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 3
- JVQKFYSAANIIPX-UHFFFAOYSA-N ethyl 2-[[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino]oxyacetate Chemical compound NC1=C(S(C)=O)C(C=NOCC(=O)OCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl JVQKFYSAANIIPX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- TVQJESWOCWAQOT-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-5-(2-ethylsulfinylethylamino)-N'-hydroxypyrazole-3-carboximidamide Chemical compound CCS(=O)CCNC1=C(S(=O)CC)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl TVQJESWOCWAQOT-UHFFFAOYSA-N 0.000 claims description 2
- PFLHOANQLAGBHX-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(ethylamino)-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound CCNC1=C(S(C)=O)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PFLHOANQLAGBHX-UHFFFAOYSA-N 0.000 claims description 2
- CGYQOERHBSIQPC-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfinyl-5-(2-methylsulfinylethylamino)pyrazole-3-carboximidamide Chemical compound CS(=O)CCNC1=C(S(C)=O)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl CGYQOERHBSIQPC-UHFFFAOYSA-N 0.000 claims description 2
- PQBREZNGZLSMSZ-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-5-(methylamino)-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound CNC1=C(S(C)=O)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PQBREZNGZLSMSZ-UHFFFAOYSA-N 0.000 claims description 2
- NZNQGXIBXIXQKM-UHFFFAOYSA-N 1-[2-bromo-6-chloro-4-(trifluoromethyl)phenyl]-5-(ethylamino)-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound CCNC1=C(S(C)=O)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Br NZNQGXIBXIXQKM-UHFFFAOYSA-N 0.000 claims description 2
- HYAGNZNYTKIFQR-UHFFFAOYSA-N 1-o-[[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino] 3-o-ethyl 2-methylpropanedioate Chemical compound NC1=C(S(C)=O)C(C=NOC(=O)C(C)C(=O)OCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HYAGNZNYTKIFQR-UHFFFAOYSA-N 0.000 claims description 2
- CPJXKPCMMJRAIF-UHFFFAOYSA-N 2-[[2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(E)-N'-hydroxycarbamimidoyl]-4-methylsulfinylpyrazol-3-yl]amino]acetamide Chemical compound N1=C(C(=N)NO)C(S(=O)C)=C(NCC(N)=O)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl CPJXKPCMMJRAIF-UHFFFAOYSA-N 0.000 claims description 2
- OCCJDLPYNUFDEI-UHFFFAOYSA-N 2-methylbutan-2-yl n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]carbamate Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)OC(C)(C)CC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl OCCJDLPYNUFDEI-UHFFFAOYSA-N 0.000 claims description 2
- YLFAECFHXDNQFD-UHFFFAOYSA-N 5-(2-cyanoethylamino)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound N#CCCNC1=C(S(=O)C)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YLFAECFHXDNQFD-UHFFFAOYSA-N 0.000 claims description 2
- CQELUNRFOMWWKY-UHFFFAOYSA-N 5-[2-(benzenesulfonyl)ethylamino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C(=N)NO)C(S(=O)C)=C1NCCS(=O)(=O)C1=CC=CC=C1 CQELUNRFOMWWKY-UHFFFAOYSA-N 0.000 claims description 2
- OVRIKYTUHVSVRW-UHFFFAOYSA-N 5-[[tert-butyl(dimethyl)silyl]oxyiminomethyl]-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-amine Chemical compound N1=C(C=NO[Si](C)(C)C(C)(C)C)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl OVRIKYTUHVSVRW-UHFFFAOYSA-N 0.000 claims description 2
- UXACXWNVAPYBBO-UHFFFAOYSA-N 5-amino-1-[2,6-dibromo-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NO)C(S(=O)C)=C(N)N1C1=C(Br)C=C(C(F)(F)F)C=C1Br UXACXWNVAPYBBO-UHFFFAOYSA-N 0.000 claims description 2
- FOCNHMJXTDTBIB-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfanyl-N'-hydroxypyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NO)C(SCC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FOCNHMJXTDTBIB-UHFFFAOYSA-N 0.000 claims description 2
- DFFCAWQKGZPZSO-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-N'-hydroxypyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NO)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DFFCAWQKGZPZSO-UHFFFAOYSA-N 0.000 claims description 2
- IOJWJCKMSATFFH-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfonyl-N'-hydroxypyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NO)C(S(=O)(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl IOJWJCKMSATFFH-UHFFFAOYSA-N 0.000 claims description 2
- VIMUGTKMGQDWRW-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-(trifluoromethylsulfanyl)pyrazole-3-carboximidamide Chemical compound NC1=C(SC(F)(F)F)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VIMUGTKMGQDWRW-UHFFFAOYSA-N 0.000 claims description 2
- ZIWYUAYEFYYQPZ-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-(trifluoromethylsulfonyl)pyrazole-3-carboximidamide Chemical compound NC1=C(S(=O)(=O)C(F)(F)F)C(C(=NO)N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZIWYUAYEFYYQPZ-UHFFFAOYSA-N 0.000 claims description 2
- QIBBFULQESCULN-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfanylpyrazole-3-carboximidamide Chemical compound N1=C(C(N)=NO)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QIBBFULQESCULN-UHFFFAOYSA-N 0.000 claims description 2
- DWVDRUFILFFHBN-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NO)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DWVDRUFILFFHBN-UHFFFAOYSA-N 0.000 claims description 2
- BIQQDKBRJMQKJU-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfonylpyrazole-3-carboximidamide Chemical compound N1=C(C(N)=NO)C(S(=O)(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl BIQQDKBRJMQKJU-UHFFFAOYSA-N 0.000 claims description 2
- MMEPXJKBWLKJDF-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-n'-methoxy-4-(trifluoromethylsulfinyl)pyrazole-3-carboximidamide Chemical compound NC1=C(S(=O)C(F)(F)F)C(C(=N)NOC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl MMEPXJKBWLKJDF-UHFFFAOYSA-N 0.000 claims description 2
- GFEYQIIAVSXMQW-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-n-methoxy-n-methyl-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound NC1=C(S(C)=O)C(C(=N)N(C)OC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GFEYQIIAVSXMQW-UHFFFAOYSA-N 0.000 claims description 2
- SWYNOTUTUWSBIM-UHFFFAOYSA-N 5-amino-1-[2-chloro-4-(trifluoromethyl)phenyl]-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NO)C(S(=O)C)=C(N)N1C1=CC=C(C(F)(F)F)C=C1Cl SWYNOTUTUWSBIM-UHFFFAOYSA-N 0.000 claims description 2
- FHXHCNOTXFVNRK-UHFFFAOYSA-N CCS(=O)(=O)CCNC1=C(S(C)=O)C(C=NO)=NN1C1=CC=C(C(F)(F)F)C=C1Cl Chemical compound CCS(=O)(=O)CCNC1=C(S(C)=O)C(C=NO)=NN1C1=CC=C(C(F)(F)F)C=C1Cl FHXHCNOTXFVNRK-UHFFFAOYSA-N 0.000 claims description 2
- KREBUHAPWLQIQN-UHFFFAOYSA-N CN(C)C1=C(SC)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound CN(C)C1=C(SC)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl KREBUHAPWLQIQN-UHFFFAOYSA-N 0.000 claims description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- GJLADTBNWWLYGU-UHFFFAOYSA-N N-[1-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]ethylidene]hydroxylamine Chemical compound NC1=C(S(C)=O)C(C(=NO)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GJLADTBNWWLYGU-UHFFFAOYSA-N 0.000 claims description 2
- QBIFNYCOQPPFIA-UHFFFAOYSA-N N-[[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfanyl-5-methylpyrazol-3-yl]methylidene]hydroxylamine Chemical compound N1=C(C=NO)C(SCC)=C(C)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QBIFNYCOQPPFIA-UHFFFAOYSA-N 0.000 claims description 2
- YJBRVLAIIKZIGL-UHFFFAOYSA-N N-[[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinyl-5-methylpyrazol-3-yl]methylidene]hydroxylamine Chemical compound N1=C(C=NO)C(S(=O)CC)=C(C)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YJBRVLAIIKZIGL-UHFFFAOYSA-N 0.000 claims description 2
- WMJVIDBFRDTMBM-UHFFFAOYSA-N N1=C(C=NO)C(S(=O)C)=C(N)N1C1=NC=C(C(F)(F)F)C=C1Cl Chemical compound N1=C(C=NO)C(S(=O)C)=C(N)N1C1=NC=C(C(F)(F)F)C=C1Cl WMJVIDBFRDTMBM-UHFFFAOYSA-N 0.000 claims description 2
- CAIGLXDFKMJIFO-UHFFFAOYSA-N N1=C(C=NO)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound N1=C(C=NO)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl CAIGLXDFKMJIFO-UHFFFAOYSA-N 0.000 claims description 2
- MWRYCXJAZROYQT-UHFFFAOYSA-N N1=C(C=NO)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl Chemical compound N1=C(C=NO)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(OC(F)(F)F)C=C1Cl MWRYCXJAZROYQT-UHFFFAOYSA-N 0.000 claims description 2
- XNHSVZVCOAPAJN-UHFFFAOYSA-N N1=C(C=NO)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound N1=C(C=NO)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XNHSVZVCOAPAJN-UHFFFAOYSA-N 0.000 claims description 2
- BDVQBRCJKYSHBM-UHFFFAOYSA-N NC1=C(SC(F)(F)F)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound NC1=C(SC(F)(F)F)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl BDVQBRCJKYSHBM-UHFFFAOYSA-N 0.000 claims description 2
- XQKZFVKEMLLKMR-UHFFFAOYSA-N NC1=C(SC(F)F)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound NC1=C(SC(F)F)C(C=NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl XQKZFVKEMLLKMR-UHFFFAOYSA-N 0.000 claims description 2
- DKJASWCFCAQESA-UHFFFAOYSA-N [(z)-[amino-[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfanyl-5-formamidopyrazol-3-yl]methylidene]amino] acetate Chemical compound N1=C(C(=N)NOC(C)=O)C(SCC)=C(NC=O)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DKJASWCFCAQESA-UHFFFAOYSA-N 0.000 claims description 2
- SPHIIJZEPXPEFF-UHFFFAOYSA-N [(z)-[amino-[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(methylamino)-4-methylsulfinylpyrazol-3-yl]methylidene]amino] acetate Chemical compound CNC1=C(S(C)=O)C(C(=N)NOC(C)=O)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SPHIIJZEPXPEFF-UHFFFAOYSA-N 0.000 claims description 2
- NFAGZYQMAOWREG-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazol-3-yl]methylidene]amino] acetate Chemical compound NC1=C(S(=O)C(F)(F)F)C(C(=N)NOC(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NFAGZYQMAOWREG-UHFFFAOYSA-N 0.000 claims description 2
- UGMVJXAFLNOFKK-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazol-3-yl]methylidene]amino] acetate Chemical compound N1=C(C(=N)NOC(C)=O)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl UGMVJXAFLNOFKK-UHFFFAOYSA-N 0.000 claims description 2
- QLNFIYSOLMFAMY-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanylpyrazol-3-yl]methylidene]amino] acetate Chemical compound N1=C(C(=N)NOC(C)=O)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QLNFIYSOLMFAMY-UHFFFAOYSA-N 0.000 claims description 2
- DYWGJJDEHGCDKD-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino] 2-bromoacetate Chemical compound N1=C(C(=N)NOC(=O)CBr)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DYWGJJDEHGCDKD-UHFFFAOYSA-N 0.000 claims description 2
- RNXPMACUPUPJLJ-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino] 2-ethylbutanoate Chemical compound NC1=C(S(C)=O)C(C(=N)NOC(=O)C(CC)CC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RNXPMACUPUPJLJ-UHFFFAOYSA-N 0.000 claims description 2
- AMYJBDFZOKPFBL-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino] benzoate Chemical compound CS(=O)C1=C(N)N(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)N=C1C(=N)NOC(=O)C1=CC=CC=C1 AMYJBDFZOKPFBL-UHFFFAOYSA-N 0.000 claims description 2
- RBZTUNROXWJJPB-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino] butanoate Chemical compound NC1=C(S(C)=O)C(C(=N)NOC(=O)CCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RBZTUNROXWJJPB-UHFFFAOYSA-N 0.000 claims description 2
- MMUWACYJBJALNO-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino] octanoate Chemical compound NC1=C(S(C)=O)C(C(=N)NOC(=O)CCCCCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl MMUWACYJBJALNO-UHFFFAOYSA-N 0.000 claims description 2
- VGGHFMYHFHXYRT-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino] propanoate Chemical compound NC1=C(S(C)=O)C(C(=N)NOC(=O)CC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VGGHFMYHFHXYRT-UHFFFAOYSA-N 0.000 claims description 2
- BWVYQTFNLNQMOW-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonylpyrazol-3-yl]methylidene]amino] acetate Chemical compound NC1=C(S(C)(=O)=O)C(C(=N)NOC(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl BWVYQTFNLNQMOW-UHFFFAOYSA-N 0.000 claims description 2
- ZPTAWEFWGMKKQD-UHFFFAOYSA-N [(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonylpyrazol-3-yl]methylidene]amino] octanoate Chemical compound NC1=C(S(C)(=O)=O)C(C(=N)NOC(=O)CCCCCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZPTAWEFWGMKKQD-UHFFFAOYSA-N 0.000 claims description 2
- WKLGNDUFDUAHAP-UHFFFAOYSA-N [[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanylpyrazol-3-yl]methylideneamino] acetate Chemical compound N1=C(C=NOC(C)=O)C(SC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl WKLGNDUFDUAHAP-UHFFFAOYSA-N 0.000 claims description 2
- MFJWNEPHTYWSPJ-UHFFFAOYSA-N [[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfanylpyrazol-3-yl]methylideneamino] methyl carbonate Chemical compound NC1=C(SC)C(C=NOC(=O)OC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl MFJWNEPHTYWSPJ-UHFFFAOYSA-N 0.000 claims description 2
- ZJZBQGAEZWVQEU-UHFFFAOYSA-N [[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino] 2-methylbenzoate Chemical compound CC1=CC=CC=C1C(=O)ON=CC1=NN(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)C(N)=C1S(C)=O ZJZBQGAEZWVQEU-UHFFFAOYSA-N 0.000 claims description 2
- OXTFFFPTYWKIIG-UHFFFAOYSA-N [[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylideneamino] methyl carbonate Chemical compound NC1=C(S(C)=O)C(C=NOC(=O)OC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl OXTFFFPTYWKIIG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- UQHJUGXOWRPPBD-UHFFFAOYSA-N ethyl n-[[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]carbamate Chemical compound NC1=C(S(C)=O)C(C(/N)=N/NC(=O)OCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl UQHJUGXOWRPPBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000006782 halocycloalkylcarbonyl group Chemical group 0.000 claims description 2
- GHMYBYMJQUYUPJ-UHFFFAOYSA-N n',5-diamino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carboximidamide Chemical compound NC1=C(S(=O)C(F)(F)F)C(C(=N)NN)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GHMYBYMJQUYUPJ-UHFFFAOYSA-N 0.000 claims description 2
- RGYKNXBCHDXJRY-UHFFFAOYSA-N n',5-diamino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NN)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RGYKNXBCHDXJRY-UHFFFAOYSA-N 0.000 claims description 2
- WHWHPILFIOTPCJ-UHFFFAOYSA-N n',5-diamino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound N1=C(C(=N)NN)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl WHWHPILFIOTPCJ-UHFFFAOYSA-N 0.000 claims description 2
- NPZQMMJSDBCEIC-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazol-3-yl]methylidene]amino]acetamide Chemical compound NC1=C(S(=O)C(F)(F)F)C(C(/N)=N/NC(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NPZQMMJSDBCEIC-UHFFFAOYSA-N 0.000 claims description 2
- SIAJCSPCRUXIAH-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-ethylsulfinylpyrazol-3-yl]methylidene]amino]acetamide Chemical compound N1=C(C(N)=NNC(C)=O)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SIAJCSPCRUXIAH-UHFFFAOYSA-N 0.000 claims description 2
- WMIPSHRZDQFNPM-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]-2,2-dimethylpropanamide Chemical compound N1=C(C(=N)NNC(=O)C(C)(C)C)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl WMIPSHRZDQFNPM-UHFFFAOYSA-N 0.000 claims description 2
- VNKXDALYMFCXLY-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]-2-ethylbutanamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)C(CC)CC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VNKXDALYMFCXLY-UHFFFAOYSA-N 0.000 claims description 2
- LLHAASGUXWCRCZ-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]-2-methylprop-2-enamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)C(=C)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl LLHAASGUXWCRCZ-UHFFFAOYSA-N 0.000 claims description 2
- QXGGYIPFKRAKCU-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]but-2-enamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)C=CC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QXGGYIPFKRAKCU-UHFFFAOYSA-N 0.000 claims description 2
- WQSJCSDDXRFPMU-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]butanamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)CCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl WQSJCSDDXRFPMU-UHFFFAOYSA-N 0.000 claims description 2
- SQGVKGAJXFWYDY-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]heptanamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)CCCCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SQGVKGAJXFWYDY-UHFFFAOYSA-N 0.000 claims description 2
- JWJPHAONNVKBRM-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]hexanamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)CCCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl JWJPHAONNVKBRM-UHFFFAOYSA-N 0.000 claims description 2
- BLZTVCYJGVCMOO-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]pentanamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)CCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl BLZTVCYJGVCMOO-UHFFFAOYSA-N 0.000 claims description 2
- TUHNSPLLTKWDEJ-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]propanamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)CC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl TUHNSPLLTKWDEJ-UHFFFAOYSA-N 0.000 claims description 2
- BAZXWQVBDMNNMY-UHFFFAOYSA-N n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]tetradecanamide Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)CCCCCCCCCCCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl BAZXWQVBDMNNMY-UHFFFAOYSA-N 0.000 claims description 2
- DYLXIEPWUKASBH-UHFFFAOYSA-N n-[[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]-2-methylpropanamide Chemical compound NC1=C(S(C)=O)C(C(/N)=N/NC(=O)C(C)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl DYLXIEPWUKASBH-UHFFFAOYSA-N 0.000 claims description 2
- RIDHVYNHCFERND-UHFFFAOYSA-N n-[[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]octanamide Chemical compound NC1=C(S(C)=O)C(C(/N)=N/NC(=O)CCCCCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RIDHVYNHCFERND-UHFFFAOYSA-N 0.000 claims description 2
- HLXANPMUVIXULC-UHFFFAOYSA-N propyl n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]carbamate Chemical compound NC1=C(S(C)=O)C(C(=N)NNC(=O)OCCC)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HLXANPMUVIXULC-UHFFFAOYSA-N 0.000 claims description 2
- RYAODUHQHIWGKZ-UHFFFAOYSA-N tert-butyl n-[(z)-[amino-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]methylidene]amino]carbamate Chemical compound N1=C(C(=N)NNC(=O)OC(C)(C)C)C(S(=O)C)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RYAODUHQHIWGKZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 49
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 2
- YHYWSYCHPRJDBY-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(2-ethylsulfonylethylamino)-N'-hydroxy-4-methylsulfinylpyrazole-3-carboximidamide Chemical compound CCS(=O)(=O)CCNC1=C(S(C)=O)C(C(=N)NO)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YHYWSYCHPRJDBY-UHFFFAOYSA-N 0.000 claims 1
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- 238000009372 pisciculture Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical class O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 210000003660 reticulum Anatomy 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000010904 stalk Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3388896P | 1996-12-24 | 1996-12-24 | |
US94637597A | 1997-10-07 | 1997-10-07 | |
PCT/EP1997/007117 WO1998028278A1 (en) | 1996-12-24 | 1997-12-18 | Pesticidal 1-arylpyrazoles |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69715911D1 DE69715911D1 (de) | 2002-10-31 |
DE69715911T2 true DE69715911T2 (de) | 2003-05-28 |
Family
ID=26710277
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69715911T Expired - Lifetime DE69715911T2 (de) | 1996-12-24 | 1997-12-18 | Pestizide 1-arylpyrazole |
Country Status (37)
Country | Link |
---|---|
US (1) | US6350771B1 (et) |
EP (1) | EP0948485B1 (et) |
JP (1) | JP2001507002A (et) |
KR (1) | KR20000062320A (et) |
CN (2) | CN1094928C (et) |
AP (1) | AP1039A (et) |
AR (2) | AR009154A1 (et) |
AT (1) | ATE224877T1 (et) |
AU (1) | AU745770B2 (et) |
BG (1) | BG64557B1 (et) |
BR (1) | BR9714187B1 (et) |
CA (1) | CA2275920C (et) |
CO (1) | CO5050290A1 (et) |
CR (1) | CR5676A (et) |
CZ (1) | CZ294765B6 (et) |
DE (1) | DE69715911T2 (et) |
DK (1) | DK0948485T3 (et) |
EA (1) | EA003186B1 (et) |
EE (1) | EE04306B1 (et) |
EG (1) | EG21703A (et) |
ES (1) | ES2179386T3 (et) |
HN (1) | HN1997000166A (et) |
HR (1) | HRP970704B1 (et) |
HU (1) | HUP0000482A3 (et) |
ID (1) | ID19261A (et) |
IL (2) | IL154005A0 (et) |
MA (1) | MA24431A1 (et) |
MY (1) | MY118892A (et) |
NZ (1) | NZ336419A (et) |
OA (1) | OA11299A (et) |
PA (1) | PA8443401A1 (et) |
PL (1) | PL197799B1 (et) |
SK (1) | SK283823B6 (et) |
TR (1) | TR199901472T2 (et) |
TW (1) | TW476757B (et) |
UA (1) | UA72183C2 (et) |
WO (1) | WO1998028278A1 (et) |
Families Citing this family (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA9711534B (en) | 1996-12-24 | 1998-06-24 | Rhone Poulenc Agrochimie | Pesticidal 1-arylpyrazoles. |
CA2275634A1 (en) * | 1996-12-24 | 1998-07-02 | Rhone-Poulenc Agrochimie | Pesticidal 1-aryl and pyridylpyrazole derivatives |
US6350771B1 (en) | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
ZA981934B (en) * | 1997-03-10 | 1999-09-06 | Rhone Poulenc Agrochimie | Pesticidal 1-aryl-3-iminopyrazoles. |
US6531501B1 (en) | 1998-12-11 | 2003-03-11 | Aventis Cropscience, S.A. | Control of arthropods in animals |
AR021608A1 (es) * | 1998-12-11 | 2002-07-31 | Merial Ltd | Represion de artropodos en animales |
BR0015945A (pt) | 1999-12-02 | 2002-11-12 | Aventis Cropscience Sa | Controle de artrópodos em animais |
US6531478B2 (en) * | 2000-02-24 | 2003-03-11 | Cheryl P. Kordik | Amino pyrazole derivatives useful for the treatment of obesity and other disorders |
IL163790A0 (en) | 2002-03-05 | 2005-12-18 | Bayer Cropscience Sa | 5-Substituted-alkylaminopyrazole derivatives as pesticides |
JP2005530701A (ja) * | 2002-03-05 | 2005-10-13 | バイエル・クロップサイエンス・ソシエテ・アノニム | 農薬としての5−置換アルキルアミノピラゾール誘導体 |
MXPA05005900A (es) | 2002-12-03 | 2005-08-29 | Bayer Cropscience Sa | Derivados plaguicidas de 1-aril-3-amidoxima-pirazoles. |
CA2511646A1 (en) * | 2002-12-27 | 2004-07-22 | Chiron Corporation | Thiosemicarbazones as anti-virals and immunopotentiators |
WO2005023775A1 (en) * | 2003-09-04 | 2005-03-17 | Bayer Cropscience S.A. | Pesticides |
AU2005223483B2 (en) | 2004-03-18 | 2009-04-23 | Zoetis Llc | N-(1-arylpyrazol-4l)sulfonamides and their use as parasiticides |
TW200633997A (en) * | 2004-12-08 | 2006-10-01 | Nissan Chemical Ind Ltd | Substituted heterocyclic compounds and thrombopoietin receptor activators |
TW200633998A (en) * | 2004-12-08 | 2006-10-01 | Nissan Chemical Ind Ltd | Substituted heterocyclic compounds and thrombopoietin receptor activators |
MX2007008837A (es) | 2005-01-21 | 2008-01-22 | Merial Ltd | Compuestos quimicos, procesos para su preparacion y uso de los mismos. |
AU2012203942B2 (en) * | 2006-07-05 | 2014-11-27 | Boehringer Ingelheim Animal Health USA Inc. | 1-aryl-5-alkyl pyrazole derivative compounds, processes of making and methods of using thereof |
PL2035390T3 (pl) * | 2006-07-05 | 2016-06-30 | Merial Inc | Związki będące pochodnymi 1-arylo-5-alkilopirazolu, sposoby ich wytwarzania i zastosowania |
DE102006061538A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Kombinationsprodukt zur Bekämpfung von Parasiten an Tieren |
DE102006061537A1 (de) | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
CN102271672B (zh) | 2008-11-19 | 2015-02-04 | 梅里亚有限公司 | 用于治疗寄生物感染的包含单独的或与甲脒组合的1-芳基吡唑的组合物 |
US9173728B2 (en) | 2008-11-19 | 2015-11-03 | Merial Inc. | Multi-cavity container having offset indentures for dispensing fluids |
MX2012001170A (es) | 2009-07-30 | 2012-07-20 | Merial Ltd | Compuestos de 4-amino-tieno [2,3-d]pirimidina insecticidas y metodos para su uso. |
UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
BR112013033914A2 (pt) | 2011-06-30 | 2016-11-22 | Hansen Ab Gmbh | agente para o controle de parasitas em animais e uso de um agente |
JP6249568B2 (ja) | 2011-11-17 | 2017-12-20 | メリアル インコーポレイテッド | アリールピラゾールと置換イミダゾールを含む組成物、その使用方法 |
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TWI579274B (zh) * | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備1-芳基-5-烷基吡唑化合物的改良方法 |
BR112014026746A2 (pt) * | 2012-04-27 | 2017-06-27 | Dow Agrosciences Llc | composições pesticidas e processos relacionados com as mesmas |
US9719206B2 (en) | 2012-09-14 | 2017-08-01 | Under Armour, Inc. | Apparel with heat retention layer and method of making the same |
USD765427S1 (en) | 2013-03-11 | 2016-09-06 | Under Armour, Inc. | Upper body garment with areas of interior surface ornamentation |
USD758745S1 (en) | 2013-03-11 | 2016-06-14 | Under Armour, Inc. | Lower body garment with outer surface ornamentation |
USD766599S1 (en) | 2013-03-11 | 2016-09-20 | Under Armour, Inc. | Lower body garment with inner surface ornamentation |
JP2016040242A (ja) * | 2014-08-13 | 2016-03-24 | 三井化学アグロ株式会社 | 有害生物防除剤として使用される複素環化合物又はその塩 |
WO2016069983A1 (en) | 2014-10-31 | 2016-05-06 | Merial, Inc. | Parasiticidal composition comprising fipronil |
UA127459C2 (uk) * | 2015-05-18 | 2023-08-30 | Шеньян Сайнокем Аґрокемікалз Р&Д Ко., Лтд. | Сполуки заміщеного піразолу, який містить піримідиніл, їхнє одержання і застосування |
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CN107311967B (zh) * | 2017-04-25 | 2019-07-23 | 西华大学 | N-[3-(2-呋喃基)]亚丙烯基-2-氰基-3-杂环基丙烯酰肼类衍生物及其应用 |
WO2019097306A2 (en) * | 2017-11-15 | 2019-05-23 | Adama Makhteshim, Ltd. | Synthesis of 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-ethylsulfanyl-1h-pyrazole-3-carbonitrile and related compounds |
CN110092776B (zh) * | 2019-04-30 | 2021-09-07 | 南通大学 | 含吡啶联多氟吡唑结构的吡唑肟酯类化合物及其制备方法和用途 |
CN110452175A (zh) * | 2019-07-16 | 2019-11-15 | 河南衡谱分析检测技术有限公司 | 一种乙虫腈杂质的制备方法 |
CN111689943B (zh) * | 2020-06-16 | 2021-10-29 | 中南民族大学 | 一种含环状内酰胺吡唑胺肟酯衍生物及其合成方法和应用 |
CN115894374A (zh) * | 2023-02-16 | 2023-04-04 | 广州佳途科技股份有限公司 | 一种氟甲腈的制备方法及其应用 |
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